Cycling holiday villas and apartments Isle of Wight

Close

View larger map

Also consider

Europe Holidays
431300 properties
United Kingdom Holidays
49837 properties
England Holidays
35396 properties
Cottages Cornwall
2983 properties
Apartments Greater London
941 properties
Cottages Cumbria / Lake District
940 properties
Houses Devon
2810 properties
Cottages Central England / Cotswolds
940 properties
Houses Dorset
819 properties
Houses Isle of Wight
507 properties
Cottages Peak District / Derbyshire
460 properties
Houses Somerset
610 properties
Houses Kent
557 properties
Houses Sussex
770 properties
Houses Norfolk
1023 properties
Cottages Isle of Man
11 properties
Northumberland
640 properties
Houses Yorkshire / Yorkshire Dales
1496 properties
Coastal Cottages
222 properties
Holiday homes Cowes
120 properties
Villas Ventnor
102 properties
Self catering accommodation Sandown
91 properties
Villas Shanklin
86 properties

Isle of Wight

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

305 Holiday homes

Filters applied: Cycling holidays (305)

(10) Excellent 

22

Shorwell holiday cottage rental

Isle of Wight / Shorwell

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 3 km
  • Child friendly
  • Private garden
“By far the best self-catering cottage we have ever stayed at” Really enjoyed our short stay, the cottage exceeded all our expectations. Looking forward to returning for another, longer break soon.  …see more

from £99 / night

£385 - £965 / week

Book View

from £99 / night

(8) Very Good 

15

Apartment rental in Totland

Totland Bay / Totland Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
Totland Bay, beach front three bed 5 star luxury apartment sleeps up to six. Beautiful and modern, spacious interior, 2 bathrooms. Home from home comfort, wi-fi. Footsteps from the sea, unrivalled views and glorious sunsets, safe for families, parking.Fully fitted mo  …see more

from £155 / night

£500 - £1250 / week

Book View

from £155 / night

(7) Very Good 

35

Holiday home in East Cowes

Isle of Wight / East Cowes

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Nice holiday” This property well-equipped and is ideal for small family right on the waterfront lovely island to visit. we had a great holiday with plenty of things to do around the island  …see more

from £125 / night

£575 - £1375 / week

Book View

from £125 / night

(13) Very Good 

10

Holiday home in Gurnard

Isle of Wight / Gurnard

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
“Beautiful decor, well equipped kitchen with a handy supply of board games & Dvds!” The family stayed here over the May/ June half term and we had a great time. The beach house is beautiful, well equipped and always felt welcoming and cheerful-even on  …see more

from £55 / night

£385 - £1575 / week

Book View

from £55 / night

(20) Very Good 

20

Yaverland holiday chalet rental

Sandown / Yaverland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“A great place to start and end each day” This little chalet was a great place to lay our heads at the end of each long day exploring the island. It very quickly became "home". It was much better equipped than I had expected, with lots of little extras  …see more

from £32 / night

£195 - £475 / week

Book View

from £32 / night

(28) Excellent 

8

Cottage rental in Newport

Isle of Wight / Newport

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“A home away from home” This property has been beautifully refurbished and is stylish yet very homey. The beds are exceptionally comfortable which is a must after a long day trekking around the island. It is with in walking distance to the local town f  …see more

from £80 / night

£560 - £1100 / week

Book View

from £80 / night

(12) Excellent 

19

Holiday chalet in Niton

Isle of Wight / Niton

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 5 km
  • Car not necessary
“bijou, quiet, clean” Compact but everything you would need for a short break. Very clean. Lovely location. No cooker but we had one 'ping' meal using the microwave and wandered down to the local pub every other evening to eat.  …see more

from £40 / night

£240 - £425 / week

Book View

from £40 / night

(38) Excellent 

19

Holiday cottage in Newchurch

Sandown / Newchurch

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 7 km
  • Child friendly
“A truly lovely property.” If you want a peaceful holiday property in superb location then Brew House is for you, Tastefully decorated, very clean, comfortable and well equipped. The owners had left a lovely welcome pack which included scrumptious home  …see more

from £85 / night

£500 - £750 / week

Enquire View

from £85 / night

(30) Excellent 

32

Holiday apartment in Shanklin

Shanklin / Luccombe Village

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
Contemporary designed top floor flat with 2 bedroom 2 compact shower/wcs in a detached cliffside residence with parking on the edge of Shanklin, on a spectacular stretch of cliffs. 10 min walk down to the beach, secluded garden. Fully equipped open plan kitchen.The apa  …see more

from £80 / night

£400 - £630 / week

Book View

from £80 / night

(60) Excellent 

20

Ventnor holiday apartment rental

Isle of Wight / Ventnor

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.05 km
  • Child friendly
“Wished I could have stayed longer..” Thank you to Dawn and Guy for a lovely, if all too short, stay at Marina Apartments. The location was very specal, with fabulous sea views and all the amenities of Ventnor right on your doorstep, including a beach  …see more

from £75 / night

£400 - £825 / week

Book View

from £75 / night

(2) Excellent 

8

Holiday barn in Shorwell

Isle of Wight / Shorwell

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Ask about pets
  • Private garden
For those bringing bikes, surf boards and the like, a barn is available for storage.These desirable cabins nestle in downland, above the peaceful village of Shorwell, only 2 miles from yhe south coast of the Island.Footpaths alongside the cottage join the Island's  …see more

from £70 / night

£450 - £550 / week

Book View

from £70 / night

(2) Average 

30

Home rental in Nettlestone with golf nearby

Isle of Wight / Nettlestone

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“Fabulous accommodation for enjoying this lovely Island” Our party of 8 adults and 2 children had a fabulous stay at Nettlestone House; very spacious and very well presented and equipped. And the lovely garden was a bonus for both playtime and the BBQ.  …see more

from £199 / night

£995 - £1995 / week

Book View

from £199 / night

(11) Excellent 

8

Holiday log cabin with golf nearby in Whippingham

Isle of Wight / Whippingham

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Private garden
This timber built cabin makes the ideal cosy holiday retreat for two. It is well situated for exploring the whole island, and its many attractions. •The village of Whippingham is near to Queen Victoria's Osborne House, and the yachting centre of Cowes.•Pubs and res  …see more

from £75 / night

£350 - £450 / week

Book View

from £75 / night

(15) Very Good 

24

Holiday log cabin in Cowes

Isle of Wight / Cowes

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
“Peaceful views, quiet night sleeps - nice accomodation” Cedar Croft is a lovely beach lodge situated down a fairly long farm track nestling with several other chalets overlooking the solent. The directions and check in information supplied was very go  …see more

from £57 / night

£400 - £670 / week

Book View

from £57 / night

(20) Excellent 

21

Holiday apartment with golf nearby in Ventnor

Isle of Wight / Ventnor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
“Perfect holidays - nice and well equipped appartment” On arrival we immediately felt at home at Royal Marine House. 1st floor appartment is well equipped with washing machine, dishwasher, TV/DVD and of course WIFI. We loved the view from the windows  …see more

from £80 / night

£400 - £790 / week

Enquire View

from £80 / night

(18) Excellent 

12

Holiday chalet with shared pool, golf nearby in Gurnard

Isle of Wight / Gurnard

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Decorated to a high standard and spotless” We booked this chalet for one week, we stay on the Island every year in self catering accommodation and this was by far the best we have stayed in. The chalet is decorated to a high standard, it was absolutel  …see more

from £75 / night

£350 - £550 / week

Enquire View

from £75 / night

(17) Excellent 

22

Holiday cottage in Ryde

Isle of Wight / Ryde

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
“Everything you could dream of in a cottage with a sea view” We were completely impressed by how well appointed the property was - it is truly a home from home, having literally everything you could possibly need. The enclosed courtyard was real peace  …see more

from £58 / night

£300 - £800 / week

Book View

from £58 / night

(14) Excellent 

27

Holiday cottage in Brading

Isle of Wight / Brading

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
“Had a wonderful stay - Clean and Spacious with warm welcome by Colin and Julie” Colin and Julie gave us warmest welcome and made sure we have a comfortable stay. The house was spacious, kept very tidy and had everything we needed. It was nice to have  …see more

from £80 / night

£400 - £859 / week

Book View

from £80 / night

(4) Excellent 

11

Holiday home letting

Isle of Wight / Newport

3 9 1 night min

  • 3 bedrooms
  • Sleeps 9
  • 1 night min
  • Child friendly
  • Private garden
This spacious and comfortable semi-detached house is situated in a quiet residential neighbourhood within walking distance of Newport town centre. Situated at the top of a hill, the home boasts stunning views of the island and a well-kept private garden.  …see more

from £50 / night

£325 - £1930 / week

Book View

from £50 / night

(16) Excellent 

24

Holiday cottage in Shanklin

Shanklin / Old Village

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
“Perfect in every way” I stayed at the Lodge with my 90 year old Aunt. She has some mobility problems so the search for accommodation was very specific. Our needs were met perfectly. She had no trouble moving around the house or getting to and from fr  …see more

from £52 / night

£360 - £700 / week

Book View

from £52 / night

(17) Excellent 

20

Studio rental in Ventnor with golf nearby

Isle of Wight / Ventnor

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
“Perfect - Fresh and light an enjoyable holiday” Excellent location, with stunning views. Apartment well looked after, clean and tidy. A delightful holiday with all the necessary facilities. 5 Minute walk to the seaside. 5 Stars  …see more

from £80 / night

£400 - £675 / week

Enquire View

from £80 / night

(4) Excellent 

21

Holiday chalet in Wootton Bridge

Isle of Wight / Wootton Bridge

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
A unique self catering holiday in an old train ! Great for exploring the Island or just relaxing around the house watching the wildlife and the tide.Comfortable all year round and close to amenities. Off peak short lets available, please contact for more details! The pr  …see more

from £125 / night

£875 / week

Book View

from £125 / night

(14) Very Good 

23

Townhouse accommodation in Yarmouth

Yarmouth / Norton, Isle of Wight

4 6 7 nights min

  • 4 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
“This place is fantastic!” We have just spent a week at Hurst View on the Isle Of Wight, it is in an ideal spot. The ferry terminal is only 5-10mins down the road, whichwas a great stress free start to the week. The house itself is very spacious with r  …see more

from £54 / night

£378 - £970 / week

Enquire View

from £54 / night

(19) Excellent 

22

Holiday cottage in Ryde

Ryde / Appley

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
Sleeps 4, cottage has 2 bedrooms, bathroom, kitchen, lounge, conservatory dining room, patio garden & bbq  …see more

from £85 / night

£595 - £950 / week

Book View

from £85 / night

(23) Excellent 

23

Holiday home in Ventnor

Isle of Wight / Ventnor

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly
“great location. Great views.” The Perch provided myself, husband small child and mother in law with a comfortable and homely stay. The beds were comfortable and the rooms airy. The kitchen provided everything we needed and the garden although small h  …see more

from £150 / night

£495 - £895 / week

Enquire View

from £150 / night

(11) Very Good 

9

Home rental in Cowes

Cowes / West Cowes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden
“Greta location, clean, tidy house” The location of the house was fantastic. We could access the town so easily and supermarkets and fish and chip shop were literally around the corner. The house itself was great, very clean and a well equipped kitchen  …see more

from £90 / night

£450 - £1600 / week

Book View

from £90 / night

(5) Excellent 

15

Apartment rental in Knighton, Isle of Wight

Isle of Wight / Knighton, Isle of Wight

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
An individual home just brimming with character & quirky charm with exposed timbers in all the rooms. Situated in a hamlet within an area designated as an 'Area of Outstanding Natural Beauty'. Explore the local footpaths or just enjoy the country views from your balcony  …see more

from £39 / night

£275 - £395 / week

Enquire View

from £39 / night

(3) Excellent 

27

Holiday home in Shorwell

Isle of Wight / Shorwell

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 3 km
  • Child friendly
  • Private garden
A rural village holiday getaway close to the unspoilt south west cost of the Isle of Wight. New for 2015 Church View is a stylish and modern family house set in the picturesque village of Shorwell opposite its historic church and country pub. Surrounded by beautiful cou  …see more

from £100 / night

£600 - £1350 / week

Book View

from £100 / night

(12) Excellent 

13

Yaverland holiday chalet rental

Sandown / Yaverland

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
“Beautiful” Such a beautiful chalet with lots of space. Excellent location for children as they could just play out on the green. Lovely decor and a well equipped kitchen. Cannot find any faults at all, will hope to come back again next year..  …see more

from £36 / night

£250 - £485 / week

Book View

from £36 / night

(13) Excellent 

20

Holiday cottage in Bonchurch

Isle of Wight / Bonchurch

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
“The stay is worth repeating” We had a cozy stay in this little cottage. As a couple very good. Bedroom was a bit cold, due to the gale blowing at night with freezing temperaturers and snow. We adviced the owners to make a second door outside to hang t  …see more

from £100 / night

£550 - £790 / week

Book View

from £100 / night

(4) Excellent 

16

Holiday home in Sandown

Isle of Wight / Sandown

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
Central location close to town centre, beach, pier, restaurants and public houses.  …see more

from £54 / night

£240 - £631 / week

Book View

from £54 / night

24

Newchurch holiday cottage rental

Sandown / Newchurch

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
Characterful cottage on the Garlic Farm on the Isle of Wight. Perfectly placed for walking, cycling and family holidays. Guests enjoy a 10% discount in our renowned restaurant, use of tennis court and football pitch. 10 minutes from the beach by car.Peacocks, red squirr  …see more

from £175 / night

£825 - £1925 / week

Book View

from £175 / night

(17) Very Good 

7

Holiday log cabin in Gurnard

Isle of Wight / Gurnard

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
“Stunning location” We stayed here for my fiance's birthday and had a great time. The view is simply beautiful and the beach is only a 2min walk (really quiet secluded beach, we were the only 2 down there moat the time). We had a couple of issues with  …see more

from £60 / night

£420 - £550 / week

Book View

from £60 / night

(5) Excellent 

20

Holiday cottage in Cowes

Cowes / West Cowes

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Private garden
Beautiful town cottage sleeping 4 guests in the heart of Cowes Old Town with luxury welcome hamper and free parking included. Regret that this property does not accept children or pets  …see more

from £150 / night

£1050 - £2480 / week

Book View

from £150 / night

(6) Excellent 

10

Holiday barn in Shorwell

Shorwell / Billingham

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Ask about pets
  • Private garden
The new properties have been fitted out extremely tastefully with all the mod cons including wood burner stoves for those chilly evenings, loadsa logs available ! At the property there is also secure storage for bikes, kayaks & also wash down & workshop facili  …see more

from £70 / night

£450 - £550 / week

Book View

from £70 / night

(13) Very Good 

17

Holiday home in Bonchurch

Isle of Wight / Bonchurch

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
Charlton House is a beautiful home set in a private and tucked away location on the edge of the highly sought after and picturesque village of Bonchurch, adjacent to the very popular Victorian town of Ventnor. Bonchurch & Ventnor has had a fair bit of media attention re  …see more

from £250 / night

£1000 - £2000 / week

Book View

from £250 / night

(27) Very Good 

33

Holiday boathouse with golf nearby in Yarmouth

Isle of Wight / Yarmouth

2 11 Min stay varies

  • 2 bedrooms
  • Sleeps 11
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
Two stunning properties in locations second to none, and our vintage stunning Airstream!  …see more

Pricing unknown

Enquire View

Pricing unknown

(36) Excellent 

26

Holiday home in Brighstone

Isle of Wight / Brighstone

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
“Lovely spacious house” Had a very nice stay in the Mill house. We all found it relaxing with lots of children. Location of the house was good for travelling around Isle of Wight. I would recommend the rental.  …see more

from £282 / night

£1975 - £3585 / week

Enquire View

from £282 / night

(5) Excellent 

25

Holiday log cabin accommodation

Isle of Wight / Whippingham

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Fabulous little hideaway” We booked this for the weekend as a girls trip away and we wanted to stay somewhere different so this ticked all the boxes. I had emailed Fiona numerous times before our stay with various queries and she was always prompt to  …see more

from £150 / night

£550 - £1200 / week

Book View

from £150 / night

(14) Excellent 

10

Holiday cottage accommodation

Isle of Wight / Bembridge

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Highly recommended!! Gorgeous house. We want to live there.” A beautiful cottage that's deceptively large. 1 double bedroom downstairs, 1 double and a huge twin bedroom upstairs. Large downstairs wet room and a family bathroom upstairs. Kitchen is ve  …see more

from £69 / night

£480 - £900 / week

Enquire View

from £69 / night